Sodium Bicarbonate → 6-Ethenylpyridine-3-carbonitrile

HRID 1781397Notes

Reaction equation

HRID 1781397 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10]O)=[N:7][CH:8]=1)#[N:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[CH2:10])=[N:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 19045350HCID 19045350, compound

Product 1

HCID 190453106-Ethenylpyridine-3-carbonitrileYield 36.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.163 g (1.1 mmol) 5-cyano-2-(2-hydroxyethyl)pyridine and 0.029 g (0.15 mmol) p-toluenesulfonic acid hydrate in 10 mL toluene was heated to reflux for five hours in a flask equipped with a Dean-Stark trap. The cooled mixture was neutralized with 5 mL saturated sodium bicarbonate solution and extracted with ether (3×15 mL). The extract was washed with 3 mL brine, dried over sodium sulfate, and filtered. The filtrate was concentrated to give an oil which was purified by flash chromatography on silica gel elating with 1:3 ethyl acetate:hexane to give 0.052 g (36%) 5-cyano-2-vinylpyridine, mp 29°-30° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for five hours in a flask
  3. customequipped with a Dean-Stark trap
  4. extractionextracted with ether (3×15 mL)
  5. washThe extract was washed with 3 mL brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customto give an oil which
  10. customwas purified by flash chromatography on silica gel elating with 1:3 ethyl acetate

Sources & evidence

ORD record
ord-15723b5096154a8997b8fde29ebb3e38
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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